Annelated P-containing heterocycles from aryl- and hetaryl-substituted phosphonium iodonium ylides with a methoxycarbonyl-group

Phosphonium-Iodonium Ylides with Heteroatomic Groups in the Synthesis of Annelated P-Containing Heterocycles

“…In this case the N -methylpyrazolyl ring and phenyl ring, respectively, are involved in the heterocyclization, yielding to a new annelated P-containing heterocyclephosphininopyrazole 22 and phosphinoline 23 . This behavior coincides with that of the methoxycarbonyl-substituted ylide 1 (Scheme , X = S), where phosphinolines were formed together with phosphininothiophenes …”

“…This behavior coincides with that of the methoxycarbonyl-substituted ylide 1 (Scheme 1, X = S), where phosphinolines were formed together with phosphininothiophenes. 17 A plausible way of formation of the products 22 and 23 is shown in Scheme 8. This scheme is discussed in detail in our Scheme 5.…”

“…11,12 Through the investigation of the photochemical heterocyclization of mixed phosphonium-iodonium ylides 1 with compounds containing CN 13 and CC 14,15 triple bonds, we opened a new route to the relatively unknown annelated Pcontaining heterocycles 2 (Scheme 1). 16,17 The benzoyl-and methoxycarbonyl-substituted ylides 1 reacted with triple bonds under UV irradiation (366 nm). The reactions of ylides 1 with CN triple bonds afforded only the triarylphosphonium-substituted oxazoles 3c.…”

“…Through the investigation of the photochemical heterocyclization of mixed phosphonium-iodonium ylides 1 with compounds containing CN and CC , triple bonds, we opened a new route to the relatively unknown annelated P-containing heterocycles 2 (Scheme ). , …”

Iodonium ylides in organic synthesis

“…[112][113][114][115] All these cycloadditions proceed under photochemical conditions. In particular, irradiation of mixed phosphonium iodonium ylides 27 in a nitrile solution with a mercury light source (254 nm) affords the corresponding oxazole derivatives 79 in moderate yields (Scheme 27).…”